It was the summer of 2015 and Ms Kraxberger, chief marketing and creative officer for Ms Trump’s clothing and accessories brand, was not happy.
She had stood and watched, at her boss’s request, as Donald Trump descended the escalator in the gaudy lobby of Trump Tower on 16 June, deriding Mexicans as “rapists” and declaring the US “a dumping ground for everybody else’s problems”.
His candidacy for the presidency surprised them all: Ms Trump quickly summoned Ms Kraxberger to record a video which she posted on social media, proclaiming her joy at her father’s announcement.
“After his speech, we went back upstairs,” Ms Kraxberger told The Independent. “She asked what I thought. I said to her: ‘you spoke very eloquently, but I disagree with everything your father said.’
“I didn’t believe at all in what her father stood for. And I didn’t want to get involved.”
As the weeks wore on, she grew increasingly unhappy, so Ms Trump and her husband called the meeting.
“I sat down with them, and she tried to explain that her dad’s candidacy would only help their brand,” said Ms Kraxberger.
“She genuinely seemed to believe that he wouldn’t win, but that it would give them more power – more book deals, more products to sell. They are master marketers: I may not agree with them, but I can certainly appreciate that.”
Ms Kraxberger said that, in their team of 15, she was not the only one who was concerned.
Hope Hicks, a former model and PR manager who had left Hiltzik Strategies for Ms Trump’s brand the year before, ultimately switching to work full-time for Mr Trump, was also worried.
“She had been Justin Bieber’s PR, and she was really upset,” recalled Ms Kraxberger. “We had a coffee, and she didn’t want to do politics.
“She had some sort of ‘campaigning for dummies’ book on her desk. It wasn’t what she wanted at all.”
As the campaign gathered pace, Ms Kraxberger’s concern mounted: she resigned in September 2015.
At the time it maybe seemed premature.
“He wasn’t going to win!” writes Michael Wolff in his book Fire and Fury. “Or losing was winning.
“Trump would be the most famous man in the world – a martyr to crooked Hillary Clinton.”
Ms Trump and Mr Kushner, he writes, “would have transformed themselves from relatively obscure rich kids into international celebrities and brand ambassadors.”
Yet a little over a year after Mx Kraxberger’s departure, Mr Trump would indeed win the election, confounding his daughter’s prediction – and everyone else’s.
“Melania was in tears – and not of joy,” Wolff writes.
Ms Trump and Mr Kushner went, of course, with Mr Trump to the White House.
Fast forward four years, and Ms Trump, now 38, and Mr Kushner, now 39, are potentially facing another life-altering upheaval.
Ms Trump is diligently campaigning for her father, but the future is very uncertain.
If Mr Trump loses on 3 November, what will they do next?
In the years since they left New York City and relocated to Washington DC, renting a $5.5m (£4.3m) six-bedroom mansion for $15,000 a month, Ms Trump has announced the end of her clothes and accessories brand.
According to her latest financial disclosures: “All operations of the business ceased on July 31, 2018.”
Also according to her latest financial disclosures, she made at least six figures from the trust holding that business – Ivanka M. Trump Business Trust (IT Collection, LLC Holding Company) – in 2019.
Analysts with the watchdog Citizens for Ethics in Washington (CREW) say that either the closure of her business applied only to parts of her fashion brand, like clothing, or that she continued to make money off of her fashion brand after it closed down.
Her perfumes, bags and shoes are still widely available – either leftover merchandise, or foreign franchises.
Mr Kushner, meanwhile, stepped down as CEO of the family real estate firm, Kushner Companies, and does not play a role in managing the firm.
But he maintains an extensive portfolio of real estate investments through the business, which controls 23,000 units of housing overall, and that continues to make him significant sums.
In August the couple reported income of at least $36m for 2019, according to financial disclosure reports made public.
The couple’s investments, mostly in real estate, were worth at least $204m and as much as $783m, roughly the same as their maximum value of $786m in 2018.
Ms Trump herself earned $3.95m from the Trump International Hotel in Washington – the same as she earned in 2017 and 2018 – and a total for 2019 of $5.5m.
The pair could be considering a straightforward return to their previous lives: moving back to Manhattan’s Upper East Side, and picking up where they left off – her in fashion, him in real estate.
They previously lived in a Park Avenue penthouse, inside the Trump Park Avenue building – moving there around 2011. But they never actually owned the apartment. Instead they either rented it or were granted free use of it by its owner, her father.
In February 2017 the apartment, featured in Elle Decor in 2012, was sold for $15.9m to a woman named Angela Chen, who according to Forbes runs a business peddling access to Chinese officials and allegedly has ties to Chinese military intelligence.
The couple is now registered to vote at a different address in the same building – a larger penthouse on the building’s 20th floor. That apartment, Forbes reported last year, is also owned by Donald Trump’s company, Trump Park Avenue LLC.
But will they, and their three young children – Arabella, nine; Joseph, six; and four-year-old Theodore – even want to go back?
In Times Square, billboards are currently on prominent display savaging them.
He is depicted in front of a row of bodybags, grinning, arms folded, with the caption: “‘New Yorkers are going to suffer and that’s their problem’ – Jared Kushner, Vanity Fair, September 17, 2020.”
The phrase was reportedly uttered by Mr Kushner at a 21 March meeting to discuss obtaining personal protective equipment (PPE) during the Covid pandemic.
In the second of the billboards, a smiling Ms Trump shows off the death toll – “33,366 New Yorkers, 221,245 Americans”, it reads, with her striking a “game show reveal” pose.
The couple have threatened to sue The Lincoln Project, the anti-Trump group of former Republicans who paid for the billboards.
They, delighted at the publicity, described them as “entitled, out-of-touch bullies” and said their response to the billboards was “comical”.
“The level of indignant outrage Jared Kushner and Ivanka Trump have shown towards The Lincoln Project for exposing their indifference for the more than 223,000 people who have lost their lives due to their reckless mismanagement of Covid-19 is comical,” they said.
“While we truly enjoy living rent-free in their heads, their empty threats will not be taken any more seriously than we take Ivanka and Jared.
“It is unsurprising that an administration that has never had any regard or understanding of our Constitution would try to trample on our first amendment rights, but we fully intend on making this civics lesson as painful as possible.”
It is not the welcome home they would have liked.
“My advice to them would be to disappear for a year or two,” said Rob Goldstone, a British PR who worked alongside the Trumps, infamously setting up a 2016 meeting in Trump Tower between a Russian lawyer, Donald Trump Jr and Mr Kushner.
“Nobody knows what’s coming next – they could be faced with all sorts of legal issues.
“And it’ll be very tough for them in New York, where they are so disliked. They could go to Connecticut or upstate or to Florida, perhaps. You hear that people spit at them in restaurants.”
Eric Trump, Ms Trump’s younger brother, was spat at by a bartender in a Chicago restaurant last summer; a woman was charged with assaulting White House counsellor Kellyanne Conway at a Mexican restaurant in Bethesda in 2018, and former press secretary Sarah Huckabee Sanders was hounded out of a restaurant in Virginia.
“Ivanka was the darling of fashion, glamour, business – I don’t think she’s getting invited to the Met Ball any longer,” he said.
“She should do a Mariah and lay low. No one’s going to want to hear from you, and it says something that Donald has changed his official residence to Florida.”
Mr Goldstone, a former tabloid journalist who ended up on tour with Michael Jackson and doing PR for Miss Universe, told The Independent he had met Ms Trump several times at red carpet events, and was always impressed with her manner.
“You want her there at 7pm, and 6:55pm she shows up, briefed, professional, ready to go. I know that sounds mundane, but in that world she was a breath of fresh air,” he said.
“And people had high hopes for her. They thought she’d be a restraining influence on her dad, and she’s claimed to be, but she evidently wasn’t.
“There’s probably a lot of resentment from her at the fact that returning to her old life will now be so hard.”
Mr Goldstone noted they did not need, financially, to work, and have “a nice family”.
“Maybe she runs the Trump properties, writes a book or something – ‘How I Helped Make America Great Again’.
“Maybe Trump, as long rumoured, opens his own conservative news network and she works in that. Ivanka could be the new Barbara Walters, and Jared the new Roger Ailes.”
Michael D’Antonio, whose 2015 book Never Enough featured extensive interviews with Mr Trump and his ex-wife Ivana, with second ex-wife Marla Maples, Don Jr and Ms Trump, said he felt he had got “a fairly good sense of her” from his time working on the book.
“I would expect her to try and revive her brand – maybe marketing her products under just her first name,” he told The Independent.
“She could manufacture in China and sell to Red State women. She has a good sense of how to deliver appealing, almost-on-trend products to that market. So it’s $165 shoes that resemble $1,200 shoes. Businesswear for someone on a budget – and that’s a huge market.”
Mr D’Antonio said Mr Trump was “a comic book character come to life,” who was a good actor who very occasionally, with a wink, let you know he was playing the role.
“The problem is, I think he gets confused about what thought is sincere and what is part of the game. The family business is about creating fantasies – you make your money through the tax code. And for Ivanka, fashion is a good fantasy to sell.”
He said the return to New York would be jarring for her.
“Donald craved acceptance, but was such a bore he never got it,” Mr D'Antonio said. “Ivanka was accepted, but it’s gone.
“And I’ve been impressed – in a negative way – at how many characters around Jared in particular are getting into trouble. It seems they may not be so removed from the slimy underside as they like to suggest. Obviously Jared is a schemer.”
He thinks they will, despite the obstacles, try to resume their previous lives.
Ms Kraxberger, her former marketing manager, thinks she might have her sights set higher.
“I think she’s going to run for president,” she said. “They were megalomaniacs.
“She was always interested in politics – but Democrat politics.”
Ms Kraxberger said she too thinks they will return to New York.
“Their egos are stronger than their feelings,” she said.
“I have a lot of educated friends that will still support them. I’m guessing, but I don’t think she’ll lay low. I think she’ll try to leverage this.
“And God help me if she tries to do some kind of women’s campaign.”
Ms Kraxberger in 2016 attacked her former boss for promoting a federal maternity leave policy, when within her own company it was not implemented.
“When I asked about maternity leave she said she would have to think about it, that at Trump they don’t offer maternity leave and that she went back to work just a week after having her first child,” she wrote on Facebook at the time.
Now a film producer, having left behind the world of fashion and marketing, Ms Kraxberger said: “She has no idea. For her, the idea of helping us was putting us on the same healthcare plan as her housekeeper.
“And recently, when she said out of work people should find new professions? I wanted to scream. The audacity of the woman.”
While old friends like Anna Wintour – a strident critic of Donald Trump – will be long gone, Ms Trump still has a reliable network including Wendi Deng, Rupert Murdoch’s ex-wife, and her sister-in-law, model Karli Kloss.
Ms Kloss is married to Jared Kushner’s younger brother Josh, 35, and the duo are based in New York, reportedly currently hunting for an upstate retreat.
One high-ranking former diplomat, who dealt extensively with Mr Kushner on behalf of his country, said he would not be surprised to see Mr Kushner try to translate his work in the Middle East, with Mexico and Canada into a role in international affairs.
“I totally see Jared consulting on international relations for multinational corporations or governments, either as part of a big consulting group or on his own,” he told The Independent.
“Whether we agree or not, brokering the peace deals between Israel and the UAE, Bahrain and Sudan are great introduction accomplishments.”
Another UN source said, however, that he was not much liked among their colleagues.
“A lot of his work was about circumventing existing Security Council resolutions and UN processes in the Middle East,” the source said.
“He basically ignored the UN in his Middle East peace process efforts. Although he did this year brief Security Council ambassadors on his proposals, which apparently went OK.”
Mr Kushner also maintains an interest in the New York Observer – a newspaper he bought in 2006 for $10m.
He was said to have sold it to a “family trust” in 2017 but it remains a family-held company, publishing online.
Vanity Fair’s Michael Calderone, who worked for Mr Kushner at the New York Observer from 2004-7, said he doubted that his former boss would want to remain involved in international affairs, saying he was never a particularly ideological creature.
“I think there is no Kushner worldview with deep policy or political goals,” he told the podcast Inside The Hive.
“What struck me is him coming into the Observer, and thinking well, if I make this more of a business I can turn it around. It’s the same with Covid.
“He has this confidence that he sees a better way, a more efficient way of doing things. The idea that he can just take a look around and cut to the chase with these intractable solutions.”
Mr Calderone said his former boss bought the paper as a way of cementing his place in society – and he would want to return.
“Jared bought the paper at a time when he was clearly coming into his own in the world. It was a status symbol for him,” he said.
“I think he’ll come back to NYC and back to real estate, and not be knocked down by what happens. He believes he has the right way to make things work.”
A real estate insider who knows the family agreed.
“He was actively trying to do big things, and they have significant holdings,” the source told The Independent. “And he has all that sitting there waiting for him when he comes back. I cannot imagine why you’d do anything else.”
But what about fallout from his role as a de-facto vice president of an administration hated in New York City? What about his legal entanglements, and damage to his name? Won’t he be a pariah?
“Look, at all of these galas and events, most of the people there have bought their way in,” the source said. “Money talks. Half of the people in there are disgraced tycoons.
“He hires security, she joins a friendly Parents and Teachers Association or starts a charity, they donate a billion to a cause, hang out with their friends from Harvard and they are back.
“And for the lawsuits – everyone has those. It’s really not a thing. They’ll have a very nice life.”
Mr D’Antonio agrees.
“He could create the Kushner School of Policy or something, if he felt he needed to. His family bought him in to Harvard.”
He laughed: “There is no way to overestimate their gall.”
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